


Up All Night

by ThayerKerbasy



Series: The Misadventures of Growley and Squirrel [6]
Category: Supernatural
Genre: Couch Sex, Demon Dean, Dom/sub Undertones, M/M, Orgasm Delay, Post-Episode: s09e23 Do You Believe In Miracles?, Pre-Episode: s10e01 Black, Smut
Language: English
Status: Completed
Published: 2017-02-04
Updated: 2017-02-04
Packaged: 2018-09-21 21:08:16
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,781
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9566399
Author URL: https://archiveofourown.org/users/ThayerKerbasy/pseuds/ThayerKerbasy
Summary: Crowley had been left frustrated and unfulfilled, but it was no real hardship thanks to the promise of one on one time with Dean.





	

**Author's Note:**

  * For [braezenkitty](https://archiveofourown.org/users/braezenkitty/gifts).



Crowley lay in a comfortable bed with satin bedding, his every muscle relaxed. To his left was Sparky, an arm across Crowley’s chest and a leg twined around Crowley’s own, nose nuzzling Crowley’s neck while he slept. To his right was Dean, also fast asleep - likely asleep solely for the pleasure of sleeping - with an arm flung possessively over Sparky’s arm and a leg trapping Crowley’s other leg, his face buried in the pillow. Hours had passed since the two had fallen asleep on him, but the thought of moving had never once crossed his mind.

With nowhere to go and nothing to do, he allowed his mind to wander. The midnight hours filled Crowley’s head with thoughts of Dean by his side forever, ruling Hell as a team. Most might think to make Dean their mindless muscle, but Crowley knew better. Dean was intelligent in his own right - if not quite up to Crowley’s hundreds of years of experience - and quite capable of contributing pertinent insight of his own. Dean would be his equal partner and Hell would tremble at their combined might.

The fantasy continued until Crowley imagined bending Dean over his desk. That was a different sort of fantasy, and one he was more than willing to indulge in. Several hours were devoted to imagining new ways in which the two of them could scandalize Hell. Seeing as Hell had seen all manner of sin and debauchery, it required a great deal of imagination, but Crowley felt up to the task.

The ache between his thighs was a reminder of the evening’s entertainment. The pain of his stretched bollocks had faded over the hours, but the ache of denial remained. There was no doubt in his mind, Dean had known exactly what he was doing when he had outlined their sleeping arrangements. Crowley ached to touch himself, to relieve his pent up frustration, but he refrained. Remaining still, he lay with an arm wrapped around each of his bedmates, desire simmering as he fueled it intermittently with thoughts of increasingly more creative imaginary sex. A small part of his mind continued to track the time though, even throughout his most creative fantasies.

Time passed and the moon hung low in the sky. It was time to wake Dean and relocate to the downstairs sofa, but a part of Crowley would have been content to remain exactly as he was. His thumbs traced circles over his bedmates’ skin. While they were asleep, any of Crowley’s wishes were possible, in theory. Crowley was nothing if not realistic though. Sighing softly, he tapped Dean’s shoulder with a finger and whispered in his ear, “Dean?”

That was all it took to rouse Dean from his slumber. His head turned, his long-lashed eyelids blinked open and it took a moment before his lovely green eyes focussed on Crowley, then his lips curved up in a predatory smile. Without saying a word, Dean reclaimed his sprawled limbs, slid out of the bed, and beckoned to Crowley with one finger. Not bothering to wait, he then silently left the room, leaving Crowley to extricate himself from Sparky’s clinging grasp. Sparky needed his rest and Crowley had no desire to wake him. Using his natural demonic powers, Crowley held Sparky in place while he slid out of the bed. Then he slowly relaxed his hold, easing Sparky down until he was resting comfortably on his own, tucking the blanket up around his shoulders so he wouldn’t get cold all alone.

To make up for lost time, Crowley then teleported downstairs. He appeared in front of the fireplace, stark naked. Dean reclined upon a blanket on the sofa, also starkers, idly stroking himself. Crowley felt his neglected cock stirring to hardness once more at the sight of one of his fantasies made flesh. 

Upon seeing him, Dean grinned. “Well now, ain’t I a sight for sore balls. G’mornin’, sweet cheeks.”

Crowley returned Dean’s smile, thin-lipped, eyebrows raised slightly. “Good morning, love. I trust you slept well.”

Dean responded by stretching his gloriously naked body along the full length of the sofa, arms above his head, toes pointed, John Thomas brazenly standing tall. He concluded his stretch by leaving his limbs draped over the arms of the sofa. “I slept great. You? Oh, that’s right, you were up all night to get lucky. How’s that goin’ for you?”

It was difficult to feel self-conscious in a body not one’s own, but Crowley could manage all sorts of things that others found impossible. He was fully aware of the state of his bollocks, having spent the night in quiet contemplation of all things related to such, and thought that his family jewels were quite likely as blue as Dean had suggested. Never one to allow himself to get in the way of what he wanted, Crowley huffed an amused laugh. “How, exactly, do you think it’s going, sweetheart?”

Lightning quick, Dean was up and off the sofa, pinning Crowley against the fireplace mantel. “I think you were thinkin’ about my sweet ass all night. I think you hurried down here just as fast as you could, ‘cause you’re twelve kinds of desperate right now. You were right, you know. I've wanted this, but so have you. Just how long have you been chasin’ my tail?”

The fire had died down to coals, the heat from which slightly warmed the backs of his calves. With a thought, Crowley added a log to the fire and rekindled the dormant coals. Much better. He looked up into Dean’s briefly demon-black eyes and smiled the same cocky, self-assured smile he always wore. “How long? Hard to say, really. It might have been since you cuffed me and locked me in your dungeon to await your pleasure. Could be you caught my eye back when you were trapping alpha monsters for me to torture. Looking back though, I’d have to say I first began to fancy a romp with you approximately thirty seconds after you walked in my front door looking for Mister Colt’s pistol.”

Before he was halfway done speaking, Dean gave him an “are you done yet?” look. He had barely finished when Dean said, “Shut up, you talk too much,” and covered Crowley’s mouth with his own. Soft lips kissed him hard, driving all coherent thoughts from Crowley’s head. Dean’s tongue parted his lips, forceful, demanding. The stone mantel pressed against Crowley’s back, cold and rough, and it didn’t matter. All that mattered were Dean’s lips on his, entirely willing and uncoerced.

A hand slid around from Crowley’s shoulder to the back of his neck, the arm bearing the Mark of Cain still across his chest keeping him pinned, not that he intended to resist. He ran his palms down Dean’s sides, then around to pull him closer, palms pressed to the naked skin of Dean’s back. Dean’s cock pressed firmly against Crowley while his own grazed the underside of Dean’s bollocks, providing just enough contact to tease. It was perfect. 

He returned Dean’s kiss with ardor, his own tongue meeting Dean’s, further stoking his desire in a way that a contract-sealing kiss never did. The thought of kissing Dean had occupied his imagination for ages, but his imagination paled in comparison with the reality. He caught up Dean’s lower lip between his teeth, pulling away gently, his teeth lightly grazing the sensitive skin. In response, Dean’s fingers tightened on the back of his neck, then released him. 

Pulling back from the kiss and stepping aside, Dean growled, “Get over there and sit down.”

In that moment, Dean Winchester was magnificent. His hair was spiked up but in glorious disarray, his lips were pink and luscious from kissing, and the firelight reflected off his naked form in the most flattering manner. Crowley unabashedly stopped and stared, prompting Dean to add, “C’mon, we don’t got all night.”

Unfortunately, Dean was quite correct. Their hosts were probably accustomed to rising relatively early for work, and even though they had been up late, would likely still wake within the next few hours. While the five of them had all enjoyed the previous night’s _ménage à cinq_ , Crowley was determined not to share Dean with anyone this time. “Of course,” he said. Stealing just a moment longer to appreciate his own personal Adonis, Crowley acquiesced and sat on the blanket covering the sofa.

With a delightfully wicked smile, Dean joined him, straddling Crowley’s lap, one knee to either side of him on the sofa, Little Dean standing at attention and getting friendly with Crowley’s own thoroughly intrigued cock. Arms on the sofa behind Crowley’s head, Dean leaned in close so his lips brushed Crowley’s ear and softly rumbled, “Nothin’s changed. You’re gonna do everything I say, and you don’t get to come ‘til I give the word. Capice?”

Throughout his many years, Crowley had tried everything at least once, and some things many times. If he could imagine it - and he could imagine so very much - he had done it. But for the second time in one night, Dean taking charge with his deliciously gruff voice went straight to Crowley’s cock. Eyes wide, he nodded and said, “Uh huh.”

Dean traced Crowley’s ear with the tip of his tongue, then briefly suckled his earlobe, pulling off with a little pop. “Good,” he said, his breath a warm caress on Crowley’s neck. “First, you’re gonna get my motor runnin’. Now you’ve got your hands, I wanna see what you can really do.”

In one fluid motion, Dean swung his left leg around behind him and twisted to fall back onto the sofa, his right leg forcing its way in behind Crowley and his cock bouncing lightly against his belly as he flopped. Bringing his arms up to cushion behind his head, Dean wiggled in place in a clear invitation. 

Crowley didn’t need to be asked twice. Shifting to his knees, he licked and kissed his way up Dean’s inner thigh, running his fingers over the tops of Dean’s thighs as he went. Avoiding the main event, he repeated the same on the other leg, taking his time despite the proverbial ticking clock. If Dean wanted an improvement on his original performance—and with both hands, Crowley could certainly improve—then he intended to take the time to do things properly. With that in mind, he paused to ask, “If I might make a suggestion? If you were to sit upon the padded arm of the sofa and lie back, it would be better for both of us.”

With a little shrug, Dean nodded, so Crowley moved out of the way to let him get up. Once in that position, Crowley grabbed a decorative pillow to kneel on and knelt on the floor between Dean’s legs. The new position offered much more in terms of accessibility, not to mention comfort for both. 

Once Dean was settled in place, Crowley began by cupping Dean’s bollocks in one hand and stroking with the fingertips of his other hand, eliciting soft sounds of enjoyment from Dean. Continuing his ministrations and moving his fingers of his other hand for variety, Crowley slowly licked a stripe along the underside of Dean’s cock. The little intake of breath that resulted was everything he could have hoped for. The expectation that he would continue there meant, of course, that he stopped stroking Dean’s bollocks and instead circled Dean’s pretty little hole with the tip of his tongue. Dean’s immediate reaction was to softly exhale, “Fuck yeah”

It had been hours since Crowley had first opened up Dean’s back door and it seemed the Mark’s astonishing rejuvenating powers extended there as well. His tongue was denied entry by an orifice that appeared to have never accepted anything inside, let alone Crowley’s cock a mere seven hours prior. The memory of that tight heat accepting him in was still so vivid in his mind, the mere thought of it made his cock twitch with anticipation. With that spurring him on, Crowley spread Dean’s cheeks with his hands and swirled his tongue around Dean’s hole, gradually working him loose once more.

Alternating between long licks and short, darting thrusts of his tongue, the sounds from Dean grew less coherent, devolving into breathy moans. Crowley was just beginning to contemplate whether it was time to move a little north to get started on a proper nosh when Dean sat up, breathing hard. “That’s enough. Grab the lube, then get your ass back here.”

Again, a little shiver of delight passed through Crowley at the novelty of being given benign commands. Without delay, he apported the little bottle from Sparky’s bedside table into his hand, then scrambled back onto the sofa. Moving out of the way so Crowley could sit, Dean then promptly climbed back atop his lap again. Crowley’s cock was painfully hard and he felt hyperaware of every spot where Dean’s skin touched his, not least of which was the grazing contact between their family jewels. For the briefest moment, he considered binding his own pleasure as he had earlier, so he wouldn’t inadvertently disobey Dean’s command, but it somehow didn’t feel right to use his powers for that. It was fine to cheat Sparky’s commands, but not Dean’s. A thought to consider some other time.

Dean held out a hand and Crowley passed over the lube. There was a click, then Dean squeezed out enough to coat his palm. He closed the cap, set the bottle on the arm of the sofa, then reached between them and began stroking Crowley, slicking his cock with slow, leisurely strokes. It took an immense effort not to thrust into Dean’s hand and still Crowley struggled. Somewhere along the way, want had become need, and Crowley had never been needy - had never allowed it - but he needed Dean.

Far too soon, Dean released him. Bereft of his touch, Crowley fought the urge to chase after friction, but couldn’t help the soft little whimper that escaped him. Dean picked up the bottle again and handed it back to Crowley, then raised himself up so he crouched just above Crowley’s thighs. “You want a smooth ride? You got two minutes to prep me, then I’m ridin’ you like a rented mule.”

After a statement like that, Crowley desperately wanted a moment to compose himself, but that would have wasted time. Instead, he coated two fingers and immediately got to work. Normally, he would have preferred to work slowly to ensure it was done properly, but with two minutes, Crowley wiggled a finger in as deep as it would go, then worked the next one in as quickly. As soon as he had both in, he removed them and coated his fingers again to get as much lubrication as possible. By the time his two minutes had elapsed, he hadn’t accomplished nearly the stretching he would have liked, but at least Dean was adequately lubricated.

As soon as Crowley reclaimed his fingers, Dean wrapped his hand around Crowley’s cock once more. Unprepared, he groaned at Dean’s touch, to which Dean smirked and said, “You want me so fuckin’ bad, don’t you?”

It was a rhetorical question, which was for the best, since Crowley didn’t even know himself the depths of his wants and needs. He settled for an enthusiastic nod, which seemed to satisfy Dean, who grinned and said, “I know.”

Dean silently guided Crowley’s cock to his arsehole, the only sounds coming from the crackling fire. When he was lined up, he paused there. “Don’t forget, you’re on lockdown ‘til I let you off.”

Again, Crowley nodded. Dean didn’t wait for him to respond further, choosing that moment to sink down. His half-stretched hole widened to accommodate Crowley, agonizingly slow. Crowley gripped the blanket to either side of him to ground himself while Dean rocked down onto Crowley’s cock. With one hand on Crowley’s shaft and the other wrapped around Crowley’s back, Dean’s gyrations were a delicious torment. Then Dean’s body surrendered, permitting Crowley entrance, and he was engulfed in warm, tight _Dean_ once more.

He was vaguely aware of the grunting noises coming from Dean, but Crowley was lost in sensation. He thought he had exaggerated his previous experience being inside Dean, but if anything it was even better than before because last time he had been in charge and rushed. This time his only job was to contain himself until he was granted release. Drawing a deep, steadying breath, Crowley released his grip on the blanket and slid his hands along Dean’s meaty thighs. It was much better than before.

A long drawn out groan drew Crowley out of his introspection. Dean had managed to work his way down until his bollocks grazed the base of Crowley’s cock. He wrapped his other arm around Crowley’s back and proceeded to make good on his promise. The pace he set would have caused lasting harm to a mortal who had been insufficiently prepped, as he had been, but thankfully Dean was no longer a mortal man.

Crowley wanted desperately to be allowed to succumb to bliss, but he was determined to obey Dean’s commands and Dean had not yet given him permission. The desire pooling in his belly had grown to a raging need that demanded release. The soft, whimpering moan that slipped past his lips did little to address his frustration, but it brought a grin to Dean’s face. 

With Crowley’s pleasure dependant on Dean, and Dean unlikely to grant his permission before unloading, Crowley needed to take matters into his own hands if he wanted to have any hope of lasting long enough. His fingers tightened on Dean’s perfectly squeezable love handles, using them exactly as the name implied. Adjusting his angle as best he could, he thrust up into Dean while trying to tamp down on his desire, in search of the sweet spot that might buy him a ticket to bliss.

Once Dean realized what Crowley was trying to do, a soft “Yessss,” fell from his lips and he leaned back a bit to help. Crowley had almost expected a reprimand, but he wasn’t going to question it. He tried to adjust the angle of his thrusts while Dean did the same until Dean’s head tipped back, a broken, “Fffffuuuu huuuhhh uuuuhhck,” heralding success.

Pleasure button located, Crowley did his best to keep nailing it while Dean held tight to him, meeting him thrust for thrust. Every time he managed direct contact, Dean moaned the most exquisitely sinful moans and Little Dean leaked sticky and wet between them. The sounds of the sofa bouncing and creaking under their combined efforts felt startlingly loud in the otherwise quiet cabin, but it suddenly didn’t matter if the sound attracted everyone within a thousand kilometers because for once, Dean and Crowley were on the same page about something and it felt incredible.

Crowley was desperate. He was sheathed to the hilt in the tightest orifice he had ever shagged, and each thrust brought him that much closer to a fulfillment he didn’t have permission to take. He closed his eyes and bit his lower lip until he drew blood. 

When he looked next, Dean was watching him, pupils blown wide. “Fuck, that’s hot.”

Without another word, Dean surged forward and kissed Crowley, running his tongue over Crowley’s bloody lip. He maintained his pace, bobbing up and down on Crowley’s cock with his own trapped between them, rubbing up against their bodies. Dean’s mouth was hot and eager and even better than before. Moaning into Dean’s mouth, Crowley took a hand off Dean’s hip and squeezed the base of his own cock in an attempt to stave off the inevitable, then reached between them to stroke Dean’s. 

Dean echoed Crowley’s moans, his lips falling slack. Crowley rubbed his thumb over the head of Dean’s cock, already so slick, then returned to stroking, his hand matching the rhythm of their bodies. Determined to last as long as he needed to, Crowley concentrated on Dean and only Dean. In a flash of insight, he thought of their first kiss earlier and specifically Dean’s reaction to teeth grazing his lip. Crowley caught up Dean’s lower lip between his teeth and nibbled, drawing another moan from Dean. That cinched it. He abandoned Dean’s mouth, moving instead to the tender spot where neck met shoulder, biting down much harder there.

The sound that dragged out of Dean was low and gutteral, almost a growl, culminating in, “Yesss!” His rhythm began to falter and his hands tightened on Crowley. “Oh god, ’s good. Now! Come for me _now_.”

No way did Crowley need to be told twice. Maintaining the pace with his hand, he thrust up into Dean and let loose, falling into ecstasy. Need and pressure gave way to pulse after pulse of relief, filling Dean with a night’s worth of pent up lust, which tipped Dean over the edge with him. Dean’s release painted a stripe up his belly and oozed down over Crowley’s fist, hot and wet. In a moment of unspoken agreement, they each leaned against the other to unnecessarily catch their breath.

The mess between them cooled and congealed, cocks softened, and words remained unspoken. Dean slid off Crowley’s lap to lay down on the sofa, cushioning his head on Crowley’s thigh and sighing contentedly. Of course Crowley could have teleported away in a puff of smoke to anywhere he wanted - Hell, a decent pub, Sparky’s bed - but that would have meant moving and he had no desire to move.

A quick gesture cleaned up the mess, another clothed Crowley in his borrowed robe, and another produced a blanket to cover Dean. Though neither of them had any need for sleep, Dean’s eyes were already closed and his breathing slowed. Crowley’s hand carded through Dean’s hair, patiently setting the disheveled mess to rights.

The birds outside had begun to sing, announcing the start of a new day, but despite all the noise, no one else in the cabin had awoken. It had been a long day and an even longer night and there were things he needed to do. There would be decisions to be made, orders to be given, not to mention his attendants would need instructions after he waved them off last night. He was a king, and kings had responsibilities. He thought about it for all of a moment before returning to running his fingers through Dean’s hair. Not bothering with flashy gestures - nobody was watching - Crowley added another log to the fire and moved the sofa closer so he could feel the heat on his toes. Hell could wait.

**Author's Note:**

> Firstly, thank you to braezenkitty for beta reading this for me. It was good the way it was, but now it's better.
> 
> Second, thank you to everyone who leaves comments and kudos after reading. You are the reason I keep writing this. Without that motivation, I probably would have stopped by now. I enjoy writing, but I enjoy it so much more when I hear from my readers.
> 
> Third, I'd like to request your opinions. I'm assuming most of you are here for the smut, but there will come a time when the plot will resume. Are you still here for that?
> 
> I'll be writing some more Juliet next, and then it'll be back to the summer of love. As always, if you enjoyed what you read, comments and kudos encourage me to keep writing. Please also feel free to come find me on Tumblr where I'm @thayerkerbasy


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